Acetone → beta-Irone

HRID 892672Notes

Reaction equation

HRID 892672 reaction equation
CC1CCC(C)C(C)(C)C=1C=O.CC(C)=O.O(C)[Na].[CH3:20][CH:21]1[C:26]([CH3:28])([CH3:27])[C@@H:25](/[CH:29]=[CH:30]/[C:31]([CH3:33])=[O:32])[C:24]([CH3:34])=[CH:23][CH2:22]1.CC1C(C)(C)[C@H](/C=C\C(C)=O)C(C)=CC1>C(O)C.CO>[CH3:20][CH:21]1[C:26]([CH3:27])([CH3:28])[C:25](/[CH:29]=[CH:30]/[C:31]([CH3:33])=[O:32])=[C:24]([CH3:34])[CH2:23][CH2:22]1

Participants

8

Reactant 5

HCID 180AcetoneHCID 6431140HCID 6431140, compoundHCID 6431141HCID 6431141, compoundHCID 144329422,5,6,6-Tetramethylcyclohex-1-ene-1-carbaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 5375215beta-IroneYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

On the other hand, addition of a solution of 3.0 g (19.74 mmol) of pure 2,5,6,6-tetramethyl-1-cyclohexen-1-carbaldehyde in 3 ml of ethanol and of 3 ml of acetone (41 mmol) to 4 ml (~22 mmol) of a 30% solution of NaOCH3 in methanol, the reaction having proceeded for 18 h at room temperature, provided, after the usual treatment and bulb-to-bulb distillation, a mixture (3.29 g) containing 34% of trans-α-irone, 6% of cis-α-irone and 50% of β-irone (yield 76%).

Workup

  1. customprovided
  2. distillationafter the usual treatment and bulb-to-bulb distillation

Sources & evidence

ORD record
ord-77f0460700d746fcb91fd2224c317a18
Source dataset
uspto-grants-1992_06
Patent number
US05118865

Reaction notes

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